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$495,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,950 Sq. Ft.
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Under contract-accepting backup offers. Welcome to this one-story 4 bed/2 Bath home, located on over 1/4 acre (0.36 acres) CORNER LOT within the CITY LIMITS of the Historical town of Winter Garden, Florida. This Ryland and Rutenburg built home, completed in 2000, has been well maintained over the years. Upon entering you are welcomed with beautiful laminate wood flooring and FRESHLY PAINTED WALLS throughout. Natural light is infused throughout the home as you walk through your Formal Dining and Living Rooms. Your kitchen is nestled in the heart of the home with an island for additional counter space, and a peninsula overlooking your Family Room. A great open floor plan for both entertaining and relaxing. Centrally located just outside of your main living areas is where you will find your screened patio and OVERSIZED FENCED YARD. This backyard can accommodate both a large pool and still have enough space to create your own OASIS in the remaining yard space! Back indoors your will find your Primary Suite offering Dual Sinks, Dual Walk-In Closets, WALK -IN SHOWER, and three additional bedrooms. ADDITIONAL UPGRADES INCLUDE: Gutters, Recently Painted Interior AND Exterior, NEW HVAC (2024), Roof (2016). NEIGHBORHOOD AMENITIES include: GATED COMMUNITY, Tennis Courts and Playground for only $92 MONTHLY. Don't miss your opportunity to live in this amazing community just moments away from shopping, hospitals, and major highways. Schedule your showing today!

Full Property Details for 2237 Wintermere Pointe Dr

General

  • Price: $495,000
  • HOA FEE: $92/month
  • HOA FEE FREQ.: Semi-Annually
  • Taxes: $3,855 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6368069
  • Updated: 12/18/2025
  • Added to Site: 32 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets
  • Appliances: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Gated, Playground
  • Security/Safety: Fire Alarm, Fire Sprinkler System, Gated Community, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Rain Gutters
  • Deck/Patio: Rear Porch, Screened
  • Porch/Patio/Deck: Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WINTERMERE POINTE
  • Driving Directions: Winter Garden Vineland Rd (CR 535) South. Turn right onto Wintermere Pointe Dr. Go through the gate, and turn left. The home will be located first house on  your left.
  • Direction Faces: Northwest

School Information

  • Elementary School: Lake Whitney Elem
  • Middle School: SunRidge Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Gated Community - No Guard, Irrigation-Reclaimed Water, Playground
  • Optional Amenities: Gated, Playground
  • Association: Yes
  • Assoc. Name: Extreme Management Team / Shelby
  • Pet Restrictions: Buyers to verify rules and regulations

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Electricity Connected, Public, Sprinkler Recycled, Water Connected

Structural Information

  • Builder: Ryland and Rutenburg
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: One
  • Square Feet: 1,950
  • Sq. Ft. Source: Public Records
  • Year Built: 2000

Lot Features

  • Lot Size (Acres): 0.36
  • Lot Size (Sq. Ft.): 15,780
  • Lot Size: 15780
  • Frontage: Street Paved
  • Street/Road Desc.: Paved
  • Fencing (Description): Fenced, Vinyl

Financial Considerations

  • Association Fee: $550
  • Assoc Fee Freq.: Semi-Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $3,855
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINTERMERE POINTE 40/88 LOT 4
  • Flood Zone Info: X
  • APN: 22327845600040
  • Property ID: 22327845600040
  • Block/Lot/Section: 88

Listed by Clock Tower Realty

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Listing agent

— 2237 Wintermere Pointe Dr —

  • Clock Tower Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2237 Wintermere Pointe Dr

School District:Orange County School District
NameGradesDistance
Lake Whitney Elementary School
1351 Windermere Road, Winter Garden, FL 34787
K-52.1 mi
SunRidge Middle School
14955 Sunridge Boulevard, Winter Garden, FL 34787
6-82.2 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2237 Wintermere Pointe Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/17/2025
Listed
$495,000
73.08%
MLS
8/26/2016
Sold
$286,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2237 Wintermere Pointe Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$3,855
—
$294,823
3%
2024
$3,855
4%
$286,514
3%
2023
$3,711
5%
$278,169
6%
2021
$3,539
-2%
$262,201
-3%
2022
$3,596
2%
$270,067
4%
2021
$3,539
2%
$258,581
2%
2019
$3,472
1%
$252,767
2%
2018
$3,438
3%
$248,054
2%
2017
$3,345
128%
$242,968
96%
2016
$1,464
-2%
$123,915
1%
2015
$1,490
-1%
$123,054
1%
2014
$1,498
3%
$122,077
1%
2013
$1,456
—
$120,273
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Clock Tower Realty

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2237 Wintermere Pointe Drive, Winter Garden, FL 34787 (MLS# O6368069) is a Single Family property with 4 bedrooms and 2 full bathrooms. 2237 Wintermere Pointe Drive is currently listed for $495,000 and was received on December 17, 2025. Want to learn more about 2237 Wintermere Pointe Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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